"One of the things that's puzzling about conflict of any kind or
competition of any kind is how often the people we expect to win
don't win. Why does America keep losing wars to people
who are a fraction of their size? How can the people of
Afghanistan have humbled the two largest superpowers in the world
in sequence?

...there's sort of countless examples of this and each time it
happens we're baffled, and what I'm trying to say is that maybe
we're only baffled because our definitions of advantage and
disadvantage are unsophisticated."

Certain privileges like wealth or military power are easy to see,
and we tend to overestimate them. The little known advantages of
the underdog, held by Afghanistan and other examples Gladwell
gave at the talk — like Steve Jobs early in his career or Israel early
in its existence — are twofold.

First,
there's a sense of desperation. Steve Jobs faced huge
competitors like Xerox, Afghanistan faced the Soviet Union and
United States. The stakes were much higher for them than for
their relatively complacent opponents, and they responded in
kind.

Also, underdogs have to
get around huge obstacles with fewer resources. While coming
up with those solutions, they learn skills those with all of the
advantages don't.

As to what we can learn from these underdogs, Gladwell
said "at the most basic level we can rearrange our
categories of what counts as an advantage and what doesn't. And
we can get over our I think unhealthy obsession with certain
kinds of privilege."